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Taxonomic group: bacteria / Proteobacteria (Phylum: Proteobacteria)
Associated disease: bacillary dysentery [ICD11: 1A02

, ICD11: XN7HG

]; infection due to Shigella flexneri [ICD11: XN7Y2

]

The structure was elucidated in this paper
NCBI PubMed ID: 15669066
Publication DOI: 10.1002/chem.200400903
Publisher: Vch Verlagsgesellschaft
Correspondence: lmulard

pasteur.fr
Institutions: Unite de Chimie Organique, URA CNRS 2128, Institut Pasteur, 28 rue du Dr Roux, 75724 Paris Cedex 15, France

The blockwise synthesis of the 2-aminoethyl glycosides of a deca- and a pentadecasaccharide made of two and three repeating units, respectively, of the Shigella flexneri serotype 2a specific polysaccharide is reported. The strategy relies on trifluoromethanesulfonic acid mediated glycosylation of a pentasaccharide building block acting as a glycosyl donor and a potential glycoside acceptor. Both targets were made available in amounts large enough for their subsequent conversion into glycoconjugates. Indeed, efficient elongation of the spacer through an acetylthioacetyl moiety and subsequent conjugation onto a Pan HLA DR-binding epitope (PADRE) T-cell-universal peptide resulted in two fully synthetic neoglycopeptides, which will be evaluated as potential vaccines against S. flexneri serotype 2a infections.

carbohydrates, Shigella flexneri, antigens, glycoconjugates, vaccines, glycopeptides

Structure type: oligomer
Location inside paper: p.1630, scheme 4, 4
Aglycon: aminoethyl
Compound class: O-antigen
Contained glycoepitopes: IEDB_125613,IEDB_125614,IEDB_127514,IEDB_130687,IEDB_133752,IEDB_133753,IEDB_133754,IEDB_135806,IEDB_135807,IEDB_135808,IEDB_135809,IEDB_135813,IEDB_135817,IEDB_135849,IEDB_136105,IEDB_137340,IEDB_141807,IEDB_141815,IEDB_141816,IEDB_142488,IEDB_143253,IEDB_144998,IEDB_146664,IEDB_151531,IEDB_153213,IEDB_225177,IEDB_885823,IEDB_983931,SB_192

Methods: 13C NMR, 1H NMR, TLC, chemical methods
Synthetic data: chemical

Related record ID(s): 30004, 30171
NCBI Taxonomy refs (TaxIDs): 42897
Reference(s) to other database(s): GTC:G23661FE
Show glycosyltransferases

There is only one chemically distinct structure:

CC(=O)N[C@H]1[C@H](O[C@H]2[C@H](O[C@H]3[C@H](O[C@@H]4[C@@H](O[C@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O)[C@H](C)O[C@@H](O[C@H]5[C@H](O)[C@@H](CO)O[C@@H](O[C@H]6[C@H](O[C@H]7[C@H](O[C@@H]8[C@@H](O[C@H]9O[C@H](CO)[C@@H](O)[C@H](O)[C@H]9O)[C@H](C)O[C@@H](O[C@H]9[C@H](O)[C@@H](CO)O[C@@H](O)[C@@H]9NC(C)=O)[C@@H]8O)O[C@@H](C)[C@H](O)[C@H]7O)O[C@@H](C)[C@H](O)[C@H]6O)[C@@H]5NC(C)=O)[C@@H]4O)O[C@@H](C)[C@H](O)[C@H]3O)O[C@@H](C)[C@H](O)[C@H]2O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@@H]1O[C@@H](C)[C@H](O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O[C@@H]2O[C@@H](C)[C@H](O)[C@@H](O)[C@H]2O[C@@H]2O[C@@H](C)[C@H](O)[C@@H](O)[C@H]2O)[C@H]1O

SVG MW SMILES 3D mol Ionize